Synthesis, resolution, and VCD analysis of an enantiopure diazaoxatricornan derivative

Journal of the American Chemical Society
Pierre MobianJérôme Lacour

Abstract

Using simple organic synthetic transformations, a novel diazaoxatricornan derivative, the 12 c-methyl-12-phenyl-8-propyl-12,12 c-dihydro-8 H-4-oxa-8,12-diazadibenzo[ cd, mn]pyrene ( 6a), was prepared. This novel chiral cup-shaped molecule was isolated in racemic form and in excellent yield after the addition of methyl lithium to the BF 4 salt of a novel unsymmetrical diazaoxatriangulenium cation. Compound 6a was found to be stable under classical laboratory conditions-something not obvious considering the extreme stability of the carbenium ion precursor, the electron-rich nature of the core, and the strain induced by the pyramidalization of the central carbon. The enantiomers were readily separated by chiral stationary phase chromatography, and the absolute configuration of (-)-( S)- 6a was determined by a comparison of the experimental and theoretical vibrational circular dichroism (VCD) spectra. This isolation of (-)-( S)- 6a and (+)-( R)- 6a constitutes thus the first report of a nonracemic closed-capped chiral bowl molecule for which the chirality is due to the intrinsic dissymmetry of the central core of the structure only.

References

Nov 25, 2000·Angewandte Chemie·B W Laursen, F C Krebs
May 15, 2001·Chemistry : a European Journal·B W Laursen, F C Krebs
Oct 25, 2001·The Journal of Organic Chemistry·P. Ulrich BiedermannIsrael Agranat
Jul 17, 2003·Angewandte Chemie·Christelle HerseJérôme Lacour
Sep 17, 2004·Angewandte Chemie·Lawrence T Scott
Feb 16, 2005·Angewandte Chemie·Benoît LaleuJérôme Lacour
Jun 30, 2005·Journal of the American Chemical Society·Ivan AprahamianMordecai Rabinovitz
Jul 30, 2005·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Bo W LaursenNiels Harrit
Aug 30, 2005·Dalton Transactions : an International Journal of Inorganic Chemistry·Marina A Petrukhina, Lawrence T Scott
Oct 3, 2006·Chemical Communications : Chem Comm·Benoît LaleuJéôrme Lacour
Dec 15, 2006·Chemical Reviews·Vikki M Tsefrikas, Lawrence T Scott
Jan 18, 2007·Journal of the American Chemical Society·Edward A JacksonLawrence T Scott
Mar 14, 2007·Journal of the American Chemical Society·Andrzej SygulaMarilyn M Olmstead
Apr 24, 2007·Angewandte Chemie·Emilio M PérezNazario Martín
May 11, 2007·The Journal of Organic Chemistry·Qiuling SongRobert A Pascal
May 17, 2007·The Journal of Organic Chemistry·Mark Mascal
Jul 20, 2007·Organic & Biomolecular Chemistry·James MackArt Sutton
Aug 2, 2007·The Journal of Organic Chemistry·Tadashi MoriYoshihisa Inoue
Aug 19, 2007·Chemical Communications : Chem Comm·Toru AmayaToshikazu Hirao
Oct 9, 2007·Journal of the American Chemical Society·Yi WangTrent H Galow

❮ Previous
Next ❯

Citations

Sep 25, 2015·Chemical Reviews·Jun Shen, Yoshio Okamoto
May 9, 2012·Chirality·Nathalie MehannaJérôme Lacour
Feb 15, 2017·Angewandte Chemie·Tomoya MiuraMasahiro Murakami
Oct 1, 2010·Chemical Society Reviews·Agnieszka Szumna
Sep 18, 2012·Chemical Communications : Chem Comm·Bin Dong, Hiromitsu Maeda
Apr 24, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Josef HamacekJérôme Lacour
Oct 7, 2015·Chemistry : a European Journal·Monika SrebroJeanne Crassous
Nov 3, 2020·Journal of Separation Science·Shouwan TangLing Huang
Mar 25, 2010·Organic Letters·Joyram GuinJérôme Lacour
Aug 14, 2009·The Journal of Organic Chemistry·Sri Kamesh NarasimhanYan-Yeung Luk
Dec 31, 2008·Journal of the American Chemical Society·Belinda BaischRainer Herges
Mar 14, 2009·The Journal of Organic Chemistry·Bo W Laursen, Thomas J Sørensen
May 3, 2019·The Journal of Organic Chemistry·Christian MertenNora M Kreienborg

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Fredrik WesterlundBo W Laursen
Angewandte Chemie
Bo W Laursen, F C Krebs
Chemical Society Reviews
Yoshio Okamoto, Tomoyuki Ikai
© 2022 Meta ULC. All rights reserved